Then you can do a 1031 exchange or sell it at a lower tax rate. 

For example, I mention that every adult must pay a $30 application fee, pass my credit/criminal background, make a combined income of 3x the rent, and whether or not the property accepts pets.

Moving out of a state with income tax to a state without before selling, saving 10% or more in taxes. 

Deduct NEW property taxes after you buyDeduct home insurance costsDeduct maintenance percentage, typically 10%Deduct vacancy+tenant nonperformance percentage(we recommend 5% for Class A, 10% Class B, 20% Class C, good luck with Class D)Deduct whatever dollar/percentage of cashflow you wantNow, what you have left over is the amount for debt service.Enter it into a mortgage calculator, with current interest rate for an investment property, to determine your maximum mortgage amount.Divide the mortgage amount by either 75% or 80%, depending on the required down payment percentage - this is your tentative price to offer.If the property needs repairs, you'll want to deduct 110%-120% of the estimated repairs from this amount.Be sure to also research the ARV and make sure it's 10-20% higher than your tentative purchase price.As long as the ARV checks out, this is the purchase price to offer.It is probably significantly below the asking price.

Can anyone recommend software which would accept monthly payments (from me to seller) and create proper 1099 forms for tax purposes at year end? 

After looking into it more, I'm concerned about potential tax implications and legal issues, such as piercing the corporate veil.

Evaluating deals on this site will help you understand expenses, income, and financial statement.

I am guessing the beach houses were usually purchased and rented with a goal of “free” family vacations being paid for (along with mortgages) by rental income.  

Not going to kill it on the rental income, but if you sell it subject to, there is a lot of equity.

However, financial freedom isn’t a one-time event; it’s about sustaining your desired lifestyle for the rest of your life.Once you have your goals, the next decision is where to invest.Investment Market/CityThe investment city determines all long-term income characteristics, including whether rents rise fast enough to outpace inflation and how long your income will last.Understanding inflation: It takes more dollars to buy the same goods every time you go to the store.